Hydrochloric Acid → tert-Butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate

HRID 909900ノート

反応式

HRID 909900 の反応式
Cl.C(N(CC)CC)C.[C:9]([C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])#[N:10].[N-:29]=[N+:30]=[N-:31].[Na+].Cl>O.C(O)(C)(C)C>[N:10]1[NH:29][N:30]=[N:31][C:9]=1[C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 58168561tert-Butyl 3-(3-cyanophenethoxy)propanoate

生成物 1

HCID 67076178tert-Butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
140 °C

実験手順

Triethylamine hydrochloride (2.09 g) was added in one portion to a mixture of tert-butyl 3-(3-cyanophenethoxy)propanoate [Example 7, Step i)] (1.74 g), sodium azide (0.99 g) and tert-butanol (12.64 mL), and sealed into a microwave tube. The reaction was heated to 140° C., over a period of 2 h in the microwave reactor. The reaction mixture was diluted with water and acidified with 2M hydrochloric acid (5 mL). The mixture was extracted with DCM and the organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane, then elution gradient 0-10% methanol in DCM to afford the subtitled compound (1.77 g). 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 7.44 (t, J=7.7 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 3.79 (t, J=5.3 Hz, 2H), 3.75 (t, J=5.6 Hz, 2H), 2.96 (t, J=5.2 Hz, 2H), 2.63 (t, J=5.3 Hz, 2H), 1.48 (s, 9H).

後処理

  1. customsealed into a microwave tube
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product
  7. customThe crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane
  8. washelution gradient 0-10% methanol in DCM

出典と根拠

ORDレコード
ord-e6eee0472922456388452656839ab281
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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